(E)-asarone

trans-1,2,4-trimethoxy-5-(1-propenyl)benzene

CAS: 2883-98-9 C12 H16 O3 MW: 208.25712000

Identification

Name(E)-asarone
IUPAC1,2,4-trimethoxy-5-[(E)-prop-1-enyl]benzene
CAS Number2883-98-9
EINECS220-743-6
FDA UNIIDQY9PNE5FK
Molecular FormulaC12 H16 O3
Molecular Weight208.25712000
MDL NumberMFCD00064457
Nikkaji NumberJ70.975A
Beilstein1910605
XlogP33.00 (est)

Regulatory

Physical Properties

Appearance white to pale yellow crystalline solid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 57.00 to 61.00 °C. @ 760.00 mm Hg
Boiling Point 296.00 to 297.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.003000 mmHg @ 25.00 °C. (est)
Flash Point 226.00 °F. TCC ( 107.70 °C. ) (est)
logP (o/w) 3.406 (est)
Soluble in alcohol
Insoluble in water

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-bird - wild LD50 750 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
IFRA Critical EffectCarcinogenicity
fragrance material specificationcis- and trans-Asarone as such should not be used as fragrance ingredients; essential oils containing cis- or trans-asarone (e.g. calamus oils) should not be used at a level such that the total concentration of cis- and trans-asarone exceeds 0.01% in consumer products.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%)Category 1: Products applied to the lips
NotesIFRA FLAVOR REQUIREMENTS:
Recommendation for (E)-asarone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

acorus tatarinowii carrot plant carrot seed cubeb oil @ 1.39% Data dianthus arenarius dianthus monspessulanus orthodon dianthera maxim. oil vietnam @ 5.70% Data

Synonyms

trans- asarabacca camphor (E)-iso asarone alpha- asarone trans- asarone trans-iso asarone trans- asarum camphor benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (E)- benzene, 1,2,4-trimethoxy-5-[(1E)-1-propen-1-yl]- benzene, 1,2,4-trimethoxy-5-[(1E)-1-propenyl]- benzene, 1,2,4-trimethoxy-5-propenyl-, (E)- etherophenol trans-1- propenyl-2,4,5-trimethoxybenzene (E)-1,2,4- trimethoxy-5-(1-propenyl) benzene (E)-1,2,4- trimethoxy-5-(1-propenyl)benzene trans-1,2,4- trimethoxy-5-(1-propenyl)benzene (E)-1,2,4- trimethoxy-5-(prop-1-en-1-yl)benzene 1,2,4- trimethoxy-5-[(1E)-1-propen-1-yl]benzene 1,2,4- trimethoxy-5-[(1E)-1-propen-1-yl]benzol 1,2,4- trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene 1,2,4- trimethoxy-5-[(E)-prop-1-enyl]benzene (E)-1,2,4- trimethoxy-5-prop-1-enylbenzene (E)-2,4,5- trimethoxypropenyl benzene trans-2,4,5- trimethoxypropenyl benzene trans-2,4,5- trimethoxypropenylbenzene PubMed: Alpha-Asarone Protects Endothelial Cells from Injury by Angiotensin II. J-Stage: Cognitive Enhancing Effects of Alpha Asarone in Amnesic Mice by Influencing Cholinergic and Antioxidant Defense Mechanisms PubMed: Identification of both GABAA receptors and voltage-activated Na(+) channels as molecular targets of anticonvulsant α-asarone. J-Stage: Anticonvulsant Activity of Acute and Chronic Treatment with a-Asarone from Acorus gramineus in Seizure Models PubMed: Comparison of the volatile oil composition of three Atalantia species. J-Stage: Cognitive enhancing effects of alpha asarone in amnesic mice by influencing cholinergic and antioxidant defense mechanisms. PubMed: Synthesis, antifeedant activity against Coleoptera and 3D QSAR study of alpha-asarone derivatives. PubMed: α-Asarone Ameliorates Memory Deficit in Lipopolysaccharide-Treated Mice via Suppression of Pro-Inflammatory Cytokines and Microglial Activation. PubMed: Systemic delivery of alpha-asarone with Kolliphor HS 15 improves its safety and therapeutic effect on asthma. PubMed: Role of Acorus calamus and alpha-asarone on hippocampal dependent memory in noise stress exposed rats. PubMed: Simultaneous Determination of Volatile Constituents from Acorus tatarinowii Schott in Rat Plasma by Gas Chromatography-Mass Spectrometry with Selective Ion Monitoring and Application in Pharmacokinetic Study. PubMed: Reversing P-glycoprotein-mediated multidrug resistance in vitro by α-asarone and β-asarone, bioactive cis-trans isomers from Acorus tatarinowii. PubMed: An overview on traditional uses and pharmacological profile of Acorus calamus Linn. (Sweet flag) and other Acorus species. PubMed: Growth-Inhibiting and morphostructural effects of constituents identified in Asarum heterotropoides root on human intestinal bacteria. PubMed: Chemical compositions, phytotoxicity, and biological activities of Acorus calamus essential oils from Nepal. PubMed: [Chemical constituents from rhizomes of Acorus tatarinowii]. PubMed: Identification of insecticidal constituents of the essential oil of Acorus calamus rhizomes against Liposcelis bostrychophila Badonnel. PubMed: Assessment of the genotoxic activity of alpha-asarone and its derivatives in the comet assay. PubMed: Development of intravenous lipid emulsion of α-asarone with significantly improved safety and enhanced efficacy. PubMed: Antidepressant-like effects of essential oil and asarone, a major essential oil component from the rhizome of Acorus tatarinowii. PubMed: Synthesis and antifeedant activity of novel alpha-asarone derivatives against stored-product pests. PubMed: Development and evaluation of α-asarone transdermal patches based on hot-melt pressure-sensitive adhesives. PubMed: Metabolism by grasshoppers of volatile chemical constituents from Mangifera indica and Solanum paniculatum leaves. PubMed: Anticonvulsant activity of acute and chronic treatment with a-asarone from Acorus gramineus in seizure models. PubMed: Comparative study of the cytotoxicity and genotoxicity of alpha- and Beta-asarone. PubMed: α-asarone from Acorus gramineus alleviates epilepsy by modulating A-type GABA receptors. PubMed: Alpha- and beta-asarone in herbal medicinal products. A case study. PubMed: Cognitive enhancing effects of alpha asarone in amnesic mice by influencing cholinergic and antioxidant defense mechanisms. PubMed: Separation of cis- and trans-Asarone from Acorus tatarinowii by Preparative Gas Chromatography. PubMed: Analysis of transformation and excretion of β-asarone in rabbits with GC-MS. PubMed: Enhanced toxicity of binary mixtures of larvicidal constituents from Asarum heterotropoides root to Culex pipiens pallens (Diptera: Culicidae). PubMed: [Study on relationship of properties and drug release rate of hot melt pressure sensitive adhesive]. PubMed: Anxiolytic-like effect of α-asarone in mice. PubMed: Alpha-Asarone incorporated in mixed micelles suitable for intravenous administration: formulation, in-vivo distribution and anaphylaxis study. PubMed: Chemical composition and biological activity of the volatile extracts of Achillea millefolium. PubMed: Chemical composition of the essential oil of aerial parts of Haussknechtia elymaitica Boiss. from Iran: a good natural source for trans-asaron. PubMed: An efficient combination of supercritical fluid extraction and high-speed counter-current chromatography to extract and purify (E)- and (Z)-diastereomers of α-asarone and β-asarone from Acorus tatarinowii Schott. PubMed: Chemical composition, antinociceptive and anti-inflammatory properties of essential oil from the roots of Illicium lanceolatum. PubMed: Discovery of gemfibrozil analogues that activate PPARα and enhance the expression of gene CPT1A involved in fatty acids catabolism. PubMed: Terpenoid composition and antifungal activity of three commercially important essential oils against Aspergillus flavus and Aspergillus niger. PubMed: Radioprotection by α-asarone: prevention of genotoxicity and hematopoietic injury in mammalian organism. PubMed: Metabolism mediated interaction of α-asarone and Acorus calamus with CYP3A4 and CYP2D6. PubMed: Development of drug-in-adhesive transdermal patch for α-asarone and in vivo pharmacokinetics and efficacy evaluation. PubMed: Neuroprotective effect of honokiol and magnolol, compounds from Magnolia officinalis, on beta-amyloid-induced toxicity in PC12 cells. PubMed: Activities of α-asarone in various animal seizure models and in biochemical assays might be essentially accounted for by antioxidant properties. PubMed: Larvicidal activity of Asarum heterotropoides root constituents against insecticide-susceptible and -resistant Culex pipiens pallens and Aedes aegypti and Ochlerotatus togoi. PubMed: Design, synthesis, and docking of highly hypolipidemic agents: Schizosaccharomyces pombe as a new model for evaluating alpha-asarone-based HMG-CoA reductase inhibitors. PubMed: Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications. PubMed: Effects of alpha-asarone on the glutamate transporter EAAC1 in Xenopus oocytes. PubMed: Neuroprotective effect of alpha-asarone on spatial memory and nitric oxide levels in rats injected with amyloid-beta((25-35)). PubMed: A high performance liquid chromatography method for simultaneous determination of rosiglitazone and gemfibrozil in human plasma. PubMed: Chemical composition, oviposition deterrent and larvicidal activities against Aedes aegypti of essential oils from Piper marginatum Jacq. (Piperaceae). PubMed: 2,4,5-trimethoxycinnamic acid: the major metabolite of alpha-asarone, retains most of the pharmacological properties of alpha-asarone. PubMed: Genotoxicity of alpha-asarone analogues. PubMed: Preparation and characterization of solid lipid nanoparticles loaded with alpha-Asarone. PubMed: [Comparison of kinetic behavior in both plasma and tissue after intravenous administration of alpha-asarone in lipid emulsion and aqueous solution in rats and mice]. PubMed: Variability in essential-oil composition of Piper marginatum sensu lato. PubMed: Rapid determination of volatile constituents in safflower by microwave distillation and simultaneous solid-phase microextraction coupled with gas chromatography-mass spectrometry. PubMed: [GC-MS analysis of essential oil from nutmeg processed by different traditional methods]. PubMed: [Studies on chemical constituents of green algae Ulva pertusa]. PubMed: [A review of recent ten-year study on alpha-asarone]. PubMed: [Study on alpha-asarone reservoir-type patch]. PubMed: In vitro acetylcholinesterase inhibitory activity of the essential oil from Acorus calamus and its main constituents. PubMed: Development of self-microemulsifying drug delivery systems for oral bioavailability enhancement of alpha-Asarone in beagle dogs. PubMed: Effect of alpha-asarone and a derivative on lipids, bile flow and Na+/K+-ATPase in ethinyl estradiol-induced cholestasis in the rat. PubMed: Hypolipidaemic and antiplatelet activity of phenoxyacetic acid derivatives related to alpha-asarone. PubMed: Fungicidal property of active component derived from Acorus gramineus rhizome against phytopathogenic fungi. PubMed: Development of gas chromatography/mass spectrometry following headspace solid-phase microextraction for fast determination of asarones in plasma. PubMed: Quantitative determination of beta-asarone in calamus by high-performance thin-layer chromatography. PubMed: 3D QSAR study of hypolipidemic asarones by comparative molecular surface analysis. PubMed: Antioxidant property of alpha-asarone against noise-stress-induced changes in different regions of rat brain. PubMed: In vitro genotoxic evaluation of three alpha-asarone analogues. PubMed: Rapid assessment of beta-asarone content of Acorus calamus by micellar electrokinetic capillary chromatography. PubMed: Molecular docking of the highly hypolipidemic agent alpha-asarone with the catalytic portion of HMG-CoA reductase. PubMed: Rapid determination of essential oil in Acorus tatarinowii Schott. by pressurized hot water extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry. PubMed: A new amide from Asarum forbesii Maxim. PubMed: [Study on GC-MS fingerprint analysis in rhizome of volatile oil of Acorus tatarinowii]. PubMed: Evaluation of analgesic and anti-inflammatory activities of Nectandra megapotamica (Lauraceae) in mice and rats. PubMed: Inhibition of cyclooxygenase (COX) enzymes by compounds from Daucus carota L. Seeds. PubMed: Essential oils from two endemic species of Apiaceae from Iran. PubMed: Alpha-asarone inhibits HMG-CoA reductase, lowers serum LDL-cholesterol levels and reduces biliary CSI in hypercholesterolemic rats. PubMed: Pest-managing efficacy of trans-asarone isolated from Daucus carota L. seeds. PubMed: Protection of cultured rat cortical neurons from excitotoxicity by asarone, a major essential oil component in the rhizomes of Acorus gramineus. PubMed: Synthesis and hypolipidemic activity of modified side chain alpha-asarone homologues. PubMed: alpha-asarone congeners as hypolipidemic agents. Pseudoreceptor versus minireceptor modeling. PubMed: Synthesis and hypolipidemic and antiplatelet activities of alpha-asarone isomers in humans (in vitro), mice (in vivo), and rats (in vivo). PubMed: Dominant lethal study of alpha-asarone in male and female mice after sub-chronic treatment. PubMed: New studies on trans-anethole oxide and trans-asarone oxide. PubMed: Synthesis and hypolipidaemic evaluation of a series of alpha-asarone analogues related to clofibrate in mice. PubMed: Comparison of GC-MS and TLC techniques for asarone isomers determination. PubMed: Dominant lethal study of alpha-asarone in male mice. PubMed: Central inhibitory effects of water extract of Acori graminei rhizoma in mice. PubMed: Hypolipidaemic activity of alpha-asarone in mice. PubMed: Structure-genotoxicity relationships of allylbenzenes and propenylbenzenes: a quantum chemical study. PubMed: [Pharmacology and toxicology of Guatteria gaumeri and alpha-asarone]. PubMed: Inhibition of lipid synthesis and secretion in long-term cultures of adult rat hepatocytes by alpha-asarone. PubMed: alpha-Asarone toxicity in long-term cultures of adult rat hepatocytes. PubMed: [Teratogenic action of alpha-asarone in the mouse]. PubMed: Sister-chromatid exchange induction produced by in vivo and in vitro exposure to alpha-asarone. PubMed: Potential allelochemicals fromPistia stratiotes L. PubMed: Central nervous system studies on an ethanol extract of Acorus calamus rhizomes. PubMed: [Antianaphylactic components of Asarum forbsii Maxin]. PubMed: [Teratogenic evaluation of alpha-asarone in the rat]. PubMed: Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1 mice. PubMed: [Research on the anticarcinogenic activation of Acorus calcamus. Anticarcinogenic activation of alpha-asarone on human carcinoma cells]. PubMed: [Asarone and its biological properties]. PubMed: Status epilepticus treated by alpha-asarone. Report of 18 cases.